CN116041380A - Silicon-containing organic compounds, mixtures, compositions and organic electronic devices - Google Patents

Silicon-containing organic compounds, mixtures, compositions and organic electronic devices Download PDF

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CN116041380A
CN116041380A CN202111249409.3A CN202111249409A CN116041380A CN 116041380 A CN116041380 A CN 116041380A CN 202111249409 A CN202111249409 A CN 202111249409A CN 116041380 A CN116041380 A CN 116041380A
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孙凖模
夏泽铭
黄增
宋晶尧
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Guangzhou Chinaray Optoelectronic Materials Ltd
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Abstract

The invention provides a silicon-containing organic compound, a mixture, a composition and an organic electronic device. The structure of the silicon-containing organic compound is shown as a general formula (1), and the silicon-containing organic compound can be used as a luminescent material in a functional layer of an electronic device, so that the efficiency and the service life of the device are improved.

Description

Silicon-containing organic compounds, mixtures, compositions and organic electronic devices
Technical Field
The invention relates to the field of organic electroluminescence, in particular to a silicon-containing organic compound, a mixture, a composition and an organic electronic device.
Background
In flat panel displays and lighting applications, organic Light Emitting Diodes (OLEDs) have the advantages of low cost, light weight, low operating voltage, high brightness, color tunability, wide viewing angle, easy assembly, and low power consumption, and thus are the most promising display technologies.
The principle of luminescence of an organic electronic device is organic electroluminescence, which refers to a phenomenon of converting electric energy into light energy by using an organic substance. Organic electroluminescent devices using organic electroluminescence generally have a positive electrode and a negative electrode, and a functional layer containing an organic substance therebetween. In order to improve the efficiency and the service life of the organic electroluminescent element, the functional layers have a multi-layer structure, and each functional layer contains different organic substances. Specifically, the light-emitting device includes a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. In an organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected from a positive electrode into an organic layer, electrons are injected from a negative electrode into the organic layer, and when the injected holes meet the electrons, excitons are formed, and light is emitted when the excitons transition back to a ground state. The organic electroluminescent element has the characteristics of self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, high responsiveness and the like.
In order to improve the luminous efficiency of the organic light emitting diode, various luminescent material systems based on fluorescence and phosphorescence have been developed. Among them, the organic light emitting diode using the fluorescent material has a characteristic of high reliability, but its internal electroluminescent quantum efficiency is limited to 25% under electrical excitation because the branching ratio of the singlet excited state and the triplet excited state of excitons is 1:3. Organic light emitting diodes using phosphorescent materials have achieved almost 100% internal electroluminescent quantum efficiency, but phosphorescent OLEDs have a great difficulty: the Roll-off effect, i.e. the luminous efficiency decreases rapidly with increasing current or brightness, is particularly disadvantageous for high brightness applications.
The phosphor materials which have practical value to date are iridium and platinum complexes, which are rare and expensive, and the complex synthesis is complicated and therefore quite costly. In order to overcome the above problems, adachi proposes the concept of reverse internal conversion, so that high efficiency comparable to phosphorescent OLEDs can be achieved with organic compounds, i.e. without using metal complexes. This concept has been achieved by various combinations of materials, such as: 1) Utilizing a composite excited state; 2) Thermally excited delayed fluorescence (TADF) materials are utilized.
The traditional red light and green light TADF materials have good results in various performances, but compared with phosphorescent light-emitting materials, the performances of the materials are still different from each other in terms of efficiency and service life.
Disclosure of Invention
Based on the above, the invention provides a silicon-containing organic compound which can be used as a luminescent material in a functional layer of an electronic device, and the luminescent efficiency and the service life of the device are prolonged.
The invention is realized by the following technical scheme.
The structure of the silicon-containing organic compound is shown as a general formula (1):
Figure BDA0003321967110000011
wherein:
X 1 、X 2 、X 3 are independently selected from CR 5 Or N, and X 1 、X 2 And X is 3 At least one of which is selected from N;
Ar 1 、Ar 2 each independently selected from a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, an alkyl group having 3 to 30 carbon atoms;
R 1 、R 2 、R 3 、R 4 、R 5 each occurrence is independently selected from: -H, -D, linear alkyl having 1 to 20C atoms, linear alkoxy having 1 to 20C atoms, linear thioalkoxy having 1 to 20C atoms, branched alkyl having 3 to 20C atoms, cyclic alkyl having 3 to 20C atoms, branched alkoxy having 3 to 20C atoms, cyclic alkoxy having 3 to 20C atoms, branched thioalkoxy having 3 to 20C atoms, cyclic thioalkoxy having 3 to 20C atoms, silyl, keto having 1 to 20C atoms, alkoxycarbonyl having 2 to 20C atoms, aryloxycarbonyl having 7 to 20C atoms, aryloxycarbonyl, Alkenyl having 1 to 20C atoms, carbamoyl, haloformyl, formyl, cyano, isocyano, thiocyanate, isothiocyanate, hydroxy, nitro, -CF 3 -Cl, -Br, -F, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms, or a combination of these groups;
n is selected from 1, 2, 3, 4 or 5;
m is selected from 1, 2, 3 or 4.
The present invention also provides a mixture comprising the silicon-containing organic compound as described above, and at least one organic functional material selected from a hole injecting material, a hole transporting material, an electron injecting material, an electron blocking material, a hole blocking material, a light emitting body, a host material, or an organic dye.
The present invention also provides a composition comprising a silicon-containing organic compound as described above or a mixture as described above, and at least one organic solvent.
The invention also provides an organic electronic device comprising a silicon-containing organic compound as described above, a mixture as described above or a functional layer prepared from a composition as described above.
Compared with the prior art, the silicon-containing organic compound has the following beneficial effects:
the D-A system provided by the invention is beneficial to improving the exciton utilization rate and the device stability of an OLED device when being used as a light-emitting object in an organic electroluminescent device, and further achieves the purposes of improving the light-emitting efficiency and prolonging the service life of the device.
Detailed Description
In order that the invention may be readily understood, a more particular description of the invention will be rendered by reference to specific embodiments that are illustrated in the appended drawings. Preferred embodiments of the present invention are shown in the examples. This invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terminology used herein in the description of the invention is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. The term "and/or" as used herein includes any and all combinations of one or more of the associated listed items.
In the present invention, the composition and the printing ink, or ink, have the same meaning and are interchangeable.
In the present invention, aromatic groups and aromatic ring systems have the same meaning and can be interchanged.
In the present invention, the heteroaromatic groups, heteroaromatic groups and heteroaromatic ring systems have the same meaning and can be interchanged.
In the present invention, "substituted" means that a hydrogen atom in a substituted group is substituted by a substituent.
In the present invention, "substituted or unsubstituted" means that the defined group may or may not be substituted. When a defined group is substituted, it is understood that the defined group may be substituted with one or more substituents R selected from, but not limited to: deuterium, cyano, isocyano, nitro or halogen, alkyl containing 1 to 20C atoms, heterocyclyl containing 3 to 20 ring atoms, aromatic containing 6 to 20 ring atoms, heteroaromatic containing 5 to 20 ring atoms, -NR' R ", silane, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, haloformyl, formyl, isocyanate, thiocyanate, isothiocyanate, hydroxyl, trifluoromethyl, and which may be further substituted with substituents acceptable in the art; it is understood that R 'and R "in-NR' R" are each independently selected from, but not limited to: H. deuterium atoms, cyano groups, isocyano groups, nitro groups or halogen groups, alkyl groups containing 1 to 10C atoms, heterocyclic groups containing 3 to 20 ring atoms, aromatic groups containing 6 to 20 ring atoms, heteroaromatic groups containing 5 to 20 ring atoms. Preferably, R is selected from, but not limited to: deuterium atoms, cyano groups, isocyano groups, nitro groups or halogen groups, alkyl groups containing 1 to 10C atoms, heterocyclic groups containing 3 to 10 ring atoms, aromatic groups containing 6 to 20 ring atoms, heteroaromatic groups containing 5 to 20 ring atoms, silane groups, carbonyl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, carbamoyl groups, haloformyl groups, formyl groups, isocyanate groups, thiocyanate groups, isothiocyanate groups, hydroxyl groups, trifluoromethyl groups, and which may be further substituted with substituents acceptable in the art.
In the present invention, the "number of ring atoms" means the number of atoms among atoms constituting the ring itself of a structural compound (for example, a monocyclic compound, a condensed ring compound, a crosslinked compound, a carbocyclic compound, a heterocyclic compound) in which atoms are bonded to form a ring. When the ring is substituted with a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. The same applies to the "number of ring atoms" described below, unless otherwise specified. For example, the number of ring atoms of the benzene ring is 6, the number of ring atoms of the naphthalene ring is 10, and the number of ring atoms of the thienyl group is 5.
"aryl or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removal of one hydrogen atom, which may be a monocyclic aryl group, or a fused ring aryl group, or a polycyclic aryl group, at least one of which is an aromatic ring system for a polycyclic species. For example, "substituted or unsubstituted aryl group having 6 to 40 ring atoms" means an aryl group having 6 to 40 ring atoms, preferably a substituted or unsubstituted aryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aryl group having 6 to 18 ring atoms, particularly preferably a substituted or unsubstituted aryl group having 6 to 14 ring atoms, and the aryl group is optionally further substituted; suitable examples include, but are not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluoranthryl, triphenylenyl, pyrenyl, perylenyl, tetracenyl, fluorenyl, perylenyl, acenaphthylenyl and derivatives thereof. It will be appreciated that a plurality of aryl groups may also be interrupted by short non-aromatic units (e.g. <10% of non-H atoms, such as C, N or O atoms), such as acenaphthene, fluorene, or 9, 9-diaryl fluorene, triarylamine, diaryl ether systems in particular should also be included in the definition of aryl groups.
"heteroaryl or heteroaromatic group" means that at least one carbon atom is replaced by a non-carbon atom on the basis of an aryl group, which may be an N atom, an O atom, an S atom, or the like. For example, "substituted or unsubstituted heteroaryl having 5 to 40 ring atoms" refers to heteroaryl having 5 to 40 ring atoms, preferably substituted or unsubstituted heteroaryl having 6 to 30 ring atoms, more preferably substituted or unsubstituted heteroaryl having 6 to 18 ring atoms, particularly preferably substituted or unsubstituted heteroaryl having 6 to 14 ring atoms, and the heteroaryl is optionally further substituted, suitable examples include, but are not limited to: : thienyl, furyl, pyrrolyl, imidazolyl, diazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, benzothienyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, furopyrrolyl, furofuranyl, thienofuranyl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, phthalazinyl, phenanthridinyl, primary pyridyl, quinazolinone, dibenzothienyl, dibenzofuranyl, carbazolyl, and derivatives thereof.
In the present invention, "alkyl" may denote a linear, branched and/or cyclic alkyl group. The carbon number of the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, adamantyl, and the like.
"halogen" or "halo" refers to F, cl, br or I.
The term "alkoxy" refers to a group having an-O-alkyl group, i.e. an alkyl group as defined above, attached to the parent core structure via an oxygen atom. Phrases containing this term, suitable examples include, but are not limited to: methoxy (-O-CH) 3 or-OMe), ethoxy (-O-CH 2 CH 3 or-OEt) and t-butoxy (-O-C (CH) 3 ) 3 or-OtBu).
In the present invention, "×" indicates a ligation site.
In the present invention, when the same group contains a plurality of substituents of the same symbol, each substituent may be the same or different from each other, for example
Figure BDA0003321967110000031
6R on benzene ring 1 May be the same or different from each other.
In the present invention, a single bond to which a substituent is attached extends through the corresponding ring, meaning that the substituent may be attached to an optional position on the ring, e.g
Figure BDA0003321967110000032
R in (2) is connected with any substitutable site of benzene ring; for example->
Figure BDA0003321967110000033
Representation->
Figure BDA0003321967110000034
Can be combined with->
Figure BDA0003321967110000035
Optionally forming a fused ring at an optional position on the benzene ring.
The invention provides a silicon-containing organic compound, which has a structure shown in a general formula (1):
Figure BDA0003321967110000036
wherein:
X 1 、X 2 、X 3 are independently selected from CR 5 Or N, and X 1 、X 2 And X is 3 At least one of which is selected from N;
Ar 1 、Ar 2 each independently selected from a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, or an alkyl group having 1 to 30 carbon atoms;
R 1 、R 2 、R 3 、R 4 、R 5 each occurrence is independently selected from: -H, -D, linear alkyl having 1 to 20C atoms, linear alkoxy having 1 to 20C atoms, linear thioalkoxy having 1 to 20C atoms, branched alkyl having 3 to 20C atoms, cyclic alkyl having 3 to 20C atoms, branched alkoxy having 3 to 20C atoms, cyclic alkoxy having 3 to 20C atoms, branched thioalkoxy having 3 to 20C atoms, cyclic thioalkoxy having 3 to 20C atoms, silyl, keto having 1 to 20C atoms, alkoxycarbonyl having 2 to 20C atoms, aryloxycarbonyl having 7 to 20C atoms, alkenyl having 1 to 20C atoms, carbamoyl, haloformyl, formyl, cyano, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, -CF 3 -Cl, -Br, -F, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms, or a combination of these groups;
n is selected from 1, 2, 3, 4 or 5;
m is selected from 1, 2, 3 or 4.
It is understood that in the present invention, m and n each represent R attached to a benzene ring 4 And R is R 3 Is a number of (3).
In a specific example, the structure of the silicon-containing organic compound is represented by general formulae (2-1) to (2-4):
Figure BDA0003321967110000041
in one example, ar 1 、Ar 2 Each independently selected from a substituted or unsubstituted aromatic group having 6 to 25 ring atoms, a substituted or unsubstituted heteroaromatic group having 6 to 25 ring atoms.
In a specific example, ar 1 、Ar 2 Each occurrence is independently selected from the group consisting of:
Figure BDA0003321967110000042
wherein:
X 4 each occurrence is independently selected from CR 6 Or N;
Y 1 are respectively and independently selected from CR 7 R 8 、NR 9 、SiR 7 R 8 、O、S、Se、S＝O、S(＝O) 2 Or PR (PR) 9 ；
R 6 、R 7 、R 8 、R 9 Each occurrence is independently selected from: -H, -D, linear alkyl having 1 to 20C atoms, linear alkoxy having 1 to 20C atoms, linear thioalkoxy having 1 to 20C atoms, branched or cyclic alkyl having 3 to 20C atoms, branched or cyclic alkoxy having 3 to 20C atoms, branched or cyclic thioalkoxy having 3 to 20C atoms, silyl, keto having 1 to 20C atoms, alkoxycarbonyl having 2 to 20C atoms, aryloxycarbonyl having 7 to 20C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, -CF 3 -Cl, -Br, -F, -I, a substituted or unsubstituted aromatic or heteroaromatic group having 5 to 20 ring atoms, an aryloxy or heteroaryloxy group having 5 to 20 ring atoms, or a combination of these groups.
Can be used forUnderstandably, when X 4 X is a binding site 4 Selected from C.
More specifically, ar 1 、Ar 2 Each occurrence is independently selected from the group consisting of:
Figure BDA0003321967110000051
wherein: * Representing the ligation site.
In a specific example, R 6 、R 7 、R 8 、R 9 Each occurrence is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 10C atoms, a branched or cyclic alkyl group having 3 to 10C atoms, cyano, nitro, -CF 3 -Cl, -Br, -F, -I, a substituted or unsubstituted aromatic or heteroaromatic group having 6 to 10 ring atoms.
More specifically, ar 1 、Ar 2 Each occurrence is independently selected from the group consisting of:
Figure BDA0003321967110000052
* Representing the ligation site.
Preferably Ar 1 、Ar 2 Each occurrence is independently selected from the group consisting of:
Figure BDA0003321967110000061
more preferably Ar 1 Selected from the group consisting of
Figure BDA0003321967110000062
Ar 2 Selected from->
Figure BDA0003321967110000063
Preferably, R 6 、R 7 、R 8 、R 9 Each timeAnd, where present, are independently selected from: -H, -D, a straight-chain alkyl group having 1 to 8C atoms, a branched or cyclic alkyl group having 3 to 8C atoms, cyano, nitro, -CF 3 -Cl, -Br, -F, -I, phenyl, biphenyl, pyridinyl, pyrimidinyl, triazinyl, naphthyl, quinolinyl, isoquinolinyl, or a combination of these groups.
Preferably X 1 、X 2 And X is 3 Selected from N.
In a specific example, R 1 、R 2 、R 3 、R 4 、R 5 Each occurrence is independently selected from: -H, -D, straight chain alkyl having 1 to 10C atoms, branched alkyl having 3 to 10C atoms, cyclic alkyl having 3 to 10C atoms, silyl, cyano, isocyano, hydroxy, nitro, -CF 3 -Cl, -Br, -F, a substituted or unsubstituted aromatic group having 6 to 20 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 20 ring atoms, or a combination of these groups.
More specifically, R 1 、R 2 Each occurrence is independently selected from: -H, -D, a straight chain alkyl group having 1 to 10C atoms, a branched chain alkyl group having 3 to 10C atoms, a cyclic alkyl group having 3 to 10C atoms, a silyl group, a cyano group, an isocyano group, a hydroxyl group, a nitro group, -CF3, -Cl, -Br, -F, a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 10 ring atoms, or a combination of these groups.
More specifically, R 1 、R 2 Each occurrence is independently selected from: -H, -D, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, adamantyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triazinyl, pyridyl, pyrimidinyl, imidazolyl, furanyl, Thienyl, benzofuranyl, benzothienyl, indolyl, carbazolyl, dibenzothienyl, dibenzofuranyl, phenyl-substituted carbazolyl, fluorenyl, alkyl-substituted fluorenyl having 1 to 10C atoms.
Preferably, R 1 And R is R 2 Selected from the same groups.
In one embodiment, R 3 Each occurrence is independently selected from: -H, -D, straight chain alkyl having 1 to 8C atoms, branched alkyl having 3 to 8C atoms, cyclic alkyl having 3 to 8C atoms, silyl, cyano, isocyano, hydroxy, nitro, -CF 3 -Cl, -Br, -F, or phenyl, or biphenyl, or pyridinyl, or pyrimidinyl, or triazinyl.
In one specific example, the silicon-containing compound is a thermally excited delayed fluorescence material.
Specifically, the silicon-containing organic compound according to the present invention is selected from the following structures but is not limited thereto:
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Figure BDA0003321967110000231
the silicon-containing organic compound can be used as an organic functional material in organic electronic devices, in particular OLED devices. The organic functional material may be selected from at least one of a Hole Injection Material (HIM), a Hole Transport Material (HTM), an Electron Transport Material (ETM), an Electron Injection Material (EIM), an Electron Blocking Material (EBM), a Hole Blocking Material (HBM), an Emitter (Emitter), a Host material (Host), and an organic dye.
In one specific example, the silicon-containing organic compound according to the present invention is used in a light-emitting layer, and preferably, can be used in a light-emitting layer as a guest material for a light-emitting layer. Preferably, the silicon-containing organic compound according to the present invention is used in a green organic electroluminescent device.
The invention further relates to a mixture comprising at least one silicon-containing organic compound as described above and at least one further organic functional material selected from the group consisting of a Hole Injection Material (HIM), a Hole Transport Material (HTM), an Electron Transport Material (ETM), an Electron Injection Material (EIM), an Electron Blocking Material (EBM), a Hole Blocking Material (HBM), a luminescent material (Emitter), a Host material (Host) and an organic dye. Details of various organic functional materials are found in WO2010135519A1, US20090134784A1 and WO 2011110277A1, the entire contents of which 3 patent documents are hereby incorporated by reference.
The invention also relates to a composition comprising at least one silicon-containing organic compound or mixture as described above, and at least one organic solvent; the at least one organic solvent is selected from aromatic or heteroaromatic, ester, aromatic ketone or aromatic ether, aliphatic ketone or aliphatic ether, alicyclic or olefinic compound, borate or phosphate compound, or mixture of two or more solvents.
In a preferred embodiment, a composition according to the invention is characterized in that the at least one organic solvent is chosen from solvents based on aromatic or heteroaromatic groups.
Examples of aromatic or heteroaromatic-based solvents suitable for the present invention are, but are not limited to: p-diisopropylbenzene, pentylbenzene, tetrahydronaphthalene, cyclohexylbenzene, chloronaphthalene, 1, 4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, pentyltoluenes, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3, 4-tetramethylbenzene, 1,2,3, 5-tetramethylbenzene, 1,2,4, 5-tetramethylbenzene, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzene, benzylbutylbenzene, dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2, 4-trichlorobenzene, 4-difluorodiphenyl methane, 1, 2-dimethoxy-4- (1-propenyl) benzene, diphenyl methane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α -dichlorodiphenyl methane, 4- (3-phenylpropyl) pyridine, benzyl benzoate, 1-bis (3, 4-dimethylphenyl) ethane, 2-isopropylnaphthalene, 2-quinolinecarboxylic acid, ethyl ester, 2-methylfuran, etc.
Examples of aromatic ketone-based solvents suitable for the present invention are, but are not limited to: 1-tetralone, 2- (phenylepoxy) tetralone, 6- (methoxy) tetralone, acetophenone, propiophenone, benzophenone, and derivatives thereof, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropionophenone, 3-methylpropionophenone, 2-methylpropionophenone, and the like.
Examples of aromatic ether-based solvents suitable for the present invention are, but are not limited to: 3-phenoxytoluene, butoxybenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1, 2-dimethoxy-4- (1-propenyl) benzene, 1, 4-benzodioxane, 1, 3-dipropylbenzene, 2, 5-dimethoxytoluene, 4-ethylben-ther, 1, 3-dipropoxybenzene, 1,2, 4-trimethoxybenzene, 4- (1-propenyl) -1, 2-dimethoxybenzene, 1, 3-dimethoxybenzene, glycidyl phenyl ether, dibenzyl ether, 4-t-butyl anisole, trans-p-propenyl anisole, 1, 2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, ethyl-2-naphthyl ether.
Suitable aliphatic ketone-based solvents for the present invention are, but are not limited to: 2-nonene, 3-nonene, 5-nonene, 2-decanone, 2, 5-adipone, 2,6, 8-trimethyl-4-nonene, fenchyl ketone, phorone, isophorone, di-n-amyl ketone, and the like; or aliphatic ethers such as amyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, and the like.
Examples of ester-based solvents suitable for the present invention are, but are not limited to: alkyl octanoates, alkyl sebacates, alkyl stearates, alkyl benzoates, alkyl phenylacetates, alkyl cinnamates, alkyl oxalates, alkyl maleates, alkyl lactones, alkyl oleates, and the like. Methyl benzoate, octyl octanoate, diethyl sebacate, diallyl phthalate, isononyl isononanoate are particularly preferred.
The solvent may be used alone or as a mixture of two or more organic solvents.
In certain preferred examples, a composition according to the invention is characterized by comprising at least one silicon-containing organic compound as described above, or a mixture and at least one organic solvent, and may further comprise another organic solvent. Examples of other organic solvents include (but are not limited to): methanol, ethanol, 2-methoxyethanol, methylene chloride, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1, 4-dioxane, acetone, methyl ethyl ketone, 1,2 dichloroethane, 3-phenoxytoluene, 1-trichloroethane, 1, 2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethylsulfoxide, tetrahydronaphthalene, decalin, indene and/or mixtures thereof.
In some preferred examples, particularly suitable solvents for the present invention are solvents having Hansen (Hansen) solubility parameters within the following ranges:
δd (dispersion force) is in the range of 17.0 to 23.2MPa1/2, particularly in the range of 18.5 to 21.0MPa 1/2;
δp (polar force) is in the range of 0.2 to 12.5MPa1/2, particularly in the range of 2.0 to 6.0MPa 1/2;
δh (hydrogen bonding force) is in the range of 0.9 to 14.2MPa1/2, particularly in the range of 2.0 to 6.0MPa 1/2.
The composition according to the invention, wherein the organic solvent is selected taking into account its boiling point parameters. In the invention, the boiling point of the organic solvent is more than or equal to 150 ℃; preferably not less than 180 ℃; more preferably not less than 200 ℃; more preferably not less than 250 ℃; and most preferably at a temperature of 275 ℃ or more or 300 ℃ or more. Boiling points in these ranges are beneficial in preventing nozzle clogging of inkjet printheads. The organic solvent may be evaporated from the solvent system to form a film comprising the functional material.
In a preferred embodiment, the composition according to the invention is a solution.
In another preferred embodiment, the composition according to the invention is a suspension.
The composition according to embodiments of the present invention may comprise 0.01wt% to 10wt% of the silicon-containing organic compound or mixture according to the present invention, preferably 0.1wt% to 5wt%, more preferably 0.2wt% to 5wt%, most preferably 0.25wt% to 3wt%.
The invention also relates to the use of said composition as a coating or printing ink for the production of organic electronic devices, particularly preferably by printing or coating.
Suitable printing or coating techniques include, but are not limited to, ink jet printing, letterpress printing, screen printing, dip coating, spin coating, doctor blade coating, roller printing, twist roller printing, lithographic printing, flexography, rotary printing, spray coating, brush or pad printing, slot die coating, and the like. Gravure printing, inkjet printing and inkjet printing are preferred. The solution or suspension may additionally include one or more components such as surface active compounds, lubricants, wetting agents, dispersants, hydrophobing agents, binders, etc., for adjusting viscosity, film forming properties, improving adhesion, etc.
The invention also provides an application of the silicon-containing organic compound, the mixture or the composition in an organic electronic device. The technical proposal is as follows:
an organic electronic device comprising a silicon-containing organic compound, a mixture, or a functional layer prepared from the above composition.
An organic electronic device comprising a first electrode, a second electrode, one or more organic functional layers between the first electrode and the second electrode, said at least one organic functional layer comprising a silicon-containing organic compound as described above, a mixture or prepared from a composition as described above.
Further, the organic electronic device comprises a cathode, an anode and at least one organic functional layer, wherein the at least one organic functional layer comprises a silicon-containing organic compound, or a mixture, or is prepared from the composition. The organic functional layer is selected from a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an emitting layer (EML), an Electron Blocking Layer (EBL), an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL); preferably, the organic functional layer is selected from light emitting layers.
The organic electronic device may be selected from, but not limited to, organic Light Emitting Diode (OLED), organic photovoltaic cell (OPV), organic light emitting cell (OLEEC), organic Field Effect Transistor (OFET), organic light emitting field effect transistor, organic laser, organic spintronic device, organic sensor and organic plasmon emitting diode (Organic Plasmon Emitting Diode), etc., and particularly preferably organic electroluminescent device such as OLED, organic light emitting field effect transistor. Particularly preferred are OLEDs.
In the light emitting device, especially the OLED, the light emitting device comprises a substrate, an anode, at least one light emitting layer and a cathode.
The substrate may be opaque or transparent. A transparent substrate may be used to fabricate a transparent light emitting device. See, for example, bulovic et al Nature 1996,380, p29, and Gu et al, appl. Phys. Lett.1996,68, p2606. The substrate may be rigid or elastic. The substrate may be plastic, metal, semiconductor wafer or glass. Preferably, the substrate has a smooth surface. Substrates without surface defects are a particularly desirable choice. In a preferred embodiment, the substrate is flexible, optionally in the form of a polymer film or plastic, having a glass transition temperature Tg of 150℃or higher, preferably over 200℃and more preferably over 250℃and most preferably over 300 ℃. Examples of suitable flexible substrates are poly (ethylene terephthalate) (PET) and polyethylene glycol (2, 6-naphthalene) (PEN).
The anode may comprise a conductive metal or metal oxide, or a conductive polymer. The anode can easily inject holes into a Hole Injection Layer (HIL) or a Hole Transport Layer (HTL) or a light emitting layer. In one embodiment, the absolute value of the difference between the work function of the anode and the HOMO level or valence band level of the emitter in the light emitting layer or of the p-type semiconductor material as HIL or HTL or Electron Blocking Layer (EBL) is less than 0.5eV, preferably less than 0.3eV, most preferably less than 0.2eV. Examples of anode materials include, but are not limited to: al, cu, au, ag, mg, fe, co, ni, mn, pd, pt, ITO aluminum doped zinc oxide (AZO), and the like. Other suitable anode materials are known and can be readily selected for use by one of ordinary skill in the art. The anode material may be deposited using any suitable technique, such as a suitable physical vapor deposition method including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like. In certain embodiments, the anode is patterned. Patterned ITO conductive substrates are commercially available and can be used to prepare devices according to the present invention.
The cathode may comprise a conductive metal or metal oxide. The cathode can easily inject electrons into the EIL or ETL or directly into the light emitting layer. In one embodiment, the absolute value of the difference between the work function of the cathode and the LUMO or conduction band level of the emitter in the light emitting layer or of the n-type semiconductor material as an Electron Injection Layer (EIL) or Electron Transport Layer (ETL) or Hole Blocking Layer (HBL) is less than 0.5eV, preferably less than 0.3eV, and most preferably less than 0.2eV. In principle, all materials which can be used as cathode of an OLED are possible as cathode materials for the device according to the invention. Examples of cathode materials include, but are not limited to: al, au, ag, ca, ba, mg, liF/Al, mgAg alloy, baF2/Al, cu, fe, co, ni, mn, pd, pt, ITO, etc. The cathode material may be deposited using any suitable technique, such as a suitable physical vapor deposition method including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like.
The OLED may further include other functional layers such as a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an Electron Blocking Layer (EBL), an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), a Hole Blocking Layer (HBL). Materials suitable for use in these functional layers are described in detail above and in WO2010135519A1, US20090134784A1 and WO2011110277A1, the entire contents of which 3 patent documents are hereby incorporated by reference.
The light emitting device according to the present invention has a light emitting wavelength of 300 to 1000nm, preferably 350 to 900nm, more preferably 400 to 800 nm.
The invention also relates to the use of an organic electronic device according to the invention in various electronic devices, including but not limited to: display devices, lighting devices, light sources, sensors, etc.
The invention also relates to an electronic device comprising an organic electronic device according to the invention, including but not limited to: display devices, lighting devices, light sources, sensors, etc.
The invention will be described in connection with preferred embodiments, but the invention is not limited to the embodiments described below, it being understood that the appended claims outline the scope of the invention and those skilled in the art, guided by the inventive concept, will recognize that certain changes made to the embodiments of the invention will be covered by the spirit and scope of the claims.
DETAILED DESCRIPTION OF EMBODIMENT (S) OF INVENTION
The silicon-containing organic compound and the method for producing the same according to the present invention are described in further detail below with reference to specific examples. The raw materials used in the following examples are all commercially available products unless otherwise specified.
1.1 Synthesis of Compounds
Example 1
The embodiment provides a silicon-containing organic compound, and the specific synthetic route is as follows:
Figure BDA0003321967110000261
synthesis of intermediate 1-1: phenoxazine (10 g,54.6 mmol), bromobenzene (17 g,109 mmol), pd was weighed out 2 (dba) 3 (1.48g,1.6mmol)，t-Bu 3 P (0.39 g,1.94 mmol), sodium t-butoxide (15.5 g,162 mmol) in a 500mL three-necked flask was reacted at 80℃for 12 hours with 200mL of toluene replaced with nitrogen. Spin-drying, washing with water, and column chromatography (eluting with PE) to obtain white solid with a yield of 80%. MS (ASAP) =259.1.
Synthesis of intermediate 1-2: in a 500ml two-necked flask, intermediate 1-1 (11 g,42.5 mmol) was placed, 200ml of DMF was added until the solid was completely dissolved, NBS (7.5 g,42.5 mmol) was weighed out and placed in a constant pressure dropping funnel, dissolved with 100ml of DMF, slowly added dropwise and reacted at room temperature for 12 hours. Spin-drying, washing with water, and column chromatography (eluting with PE) to obtain white solid with a yield of 85%. MS (ASAP) =337.0.
Synthesis of intermediate 1-3: preparing a dry 500mL three-neck flask, setting up a reaction device, vacuumizing, and introducing nitrogen; the nitrogen circulation is kept in the reaction bottle, 1, 4-dibromobenzene (10 g,42.6 mmol) is weighed, THF (250 ml) is added, the vacuum pumping and nitrogen circulation are carried out for three times, and the temperature is reduced to-78 ℃; to the flask was slowly added dropwise n-butyllithium solution (17.4 ml,42.6 mmol) and after reaction at-78℃for 30min, dimethoxydiphenylsilane (10.4 g,42.6 mmol) was rapidly added. The reaction system was allowed to slowly warm to room temperature and reacted for 12h. Water was added, extracted with DCM, and after spin-drying the solvent, a colorless oil was obtained by column chromatography (eluent PE) in 41% yield. MS (ASAP) =368.0.
Synthesis of intermediates 1-4: preparing a dry 250mL three-neck flask, setting up a reaction device, vacuumizing, and introducing nitrogen; the nitrogen circulation is kept in the reaction bottle, 1-2 (3.0 g,8.9 mmol) is weighed, THF (100 ml) is added, the vacuum pumping and nitrogen introducing are carried out for three times, and the temperature is reduced to-78 ℃; to the flask was slowly added dropwise n-butyllithium solution (3.6 ml,8.9 mmol) and after 60min reaction at-78℃1-3 (3.3 g,8.9 mmol) was added rapidly. The reaction system was allowed to slowly warm to room temperature and reacted for 12h. Water was added, extracted with DCM, and after spinning the solvent dry, PE was slurried to a white solid. The yield thereof was found to be 67%. MS (ASAP) = 595.1.
Synthesis of intermediates 1-5: weigh 1-4 (6 g,10 mmol), (Bpin) 2 (3.8g,15mmol)，AcOK(9.8g,100mmol)，Pd(dppf)Cl 2 (0.74g,1.0mmol)，t-Bu 3 P (0.39 g,1.94 mmol) was placed in a 250mL three-necked flask, 100mL of 1, 4-dioxane was added thereto, and the mixture was reacted at 100℃for 12 hours while substituting nitrogen. Spin-drying, water washing, column chromatography (eluent PE: dcm=5:1) gave a colorless oil, 93% yield. MS (ASAP) = 643.3.
Synthesis of Compound 1: 1-5 (6 g,9.3 mmol), 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (3.8 g,14 mmol), K was weighed out 2 CO 3 (12.8g,93mmol)，Pd(PPh 3 ) 4 (1.1 g,0.93 mmol) in a 250mL three-necked flask, 100mL of toluene, 50mL of ethanol, 50mL of water, and replaced with nitrogen were added and reacted at 100℃for 12 hours. Spin-drying, washing with water, column chromatography (eluent PE: dcm=3:1) gave a white solid in 50% yield. MS (ASAP) = 748.3.
Example 2
The embodiment provides a silicon-containing organic compound, and the specific synthetic route is as follows:
Figure BDA0003321967110000271
synthesis of intermediate 2-1: preparing a dry 500mL three-neck flask, setting up a reaction device, vacuumizing, and introducing nitrogen; the nitrogen circulation is kept in the reaction bottle, 1, 3-dibromobenzene (10 g,42.6 mmol) is weighed, THF (250 ml) is added, the vacuum pumping and nitrogen circulation are carried out for three times, and the temperature is reduced to-78 ℃; to the flask was slowly added dropwise n-butyllithium solution (17.4 ml,42.6 mmol) and after reaction at-78℃for 30min, dimethoxydiphenylsilane (10.4 g,42.6 mmol) was rapidly added. The reaction system was allowed to slowly warm to room temperature and reacted for 12h. Water was added, extracted with DCM, and after spin-drying the solvent, a colorless oil was obtained by column chromatography (eluent PE) in 35% yield. MS (ASAP) =368.0.
Synthesis of intermediate 2-2: preparing a dry 250mL three-neck flask, setting up a reaction device, vacuumizing, and introducing nitrogen; the nitrogen circulation is kept in the reaction bottle, 1-2 (3.0 g,8.9 mmol) is weighed, THF (100 ml) is added, the vacuum pumping and nitrogen introducing are carried out for three times, and the temperature is reduced to-78 ℃; to the flask was slowly added dropwise n-butyllithium solution (3.6 ml,8.9 mmol) and after 60min reaction at-78℃2-1 (3.3 g,8.9 mmol) was added rapidly. The reaction system was allowed to slowly warm to room temperature and reacted for 12h. Water was added, extracted with DCM, and after spinning the solvent dry, PE was slurried to a white solid. The yield thereof was found to be 55%. MS (ASAP) = 595.1.
Synthesis of intermediate 2-3: weigh 2-2 (6 g,10 mmol), (Bpin) 2 (3.8g,15mmol)，AcOK(9.8g,100mmol)，Pd(dppf)Cl 2 (0.74g,1.0mmol)，t-Bu 3 P (0.39 g,1.94 mmol) was placed in a 250mL three-necked flask, 100mL of 1, 4-dioxane was added thereto, and the mixture was reacted at 100℃for 12 hours while substituting nitrogen. Spin-drying, water washing, column chromatography (eluent PE: dcm=5:1) gave a colorless oil in 70% yield. MS (ASAP) = 643.3.
Synthesis of Compound 2: 2-3 (6 g,9.3 mmol), 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (3.8 g,14 mmol), K was weighed out 2 CO 3 (12.8g,93mmol)，Pd(PPh 3 ) 4 (1.1 g,0.93 mmol) in a 250mL three-necked flask, 100mL of toluene, 50mL of ethanol, 50mL of water, and replaced with nitrogen were added and reacted at 100℃for 12 hours. Spin-drying, washing with water, column chromatography (eluent PE: dcm=3:1) gave a white solid in 50% yield. MS (ASAP) = 748.3.
Example 3
The embodiment provides a silicon-containing organic compound, and the specific synthetic route is as follows:
Figure BDA0003321967110000272
synthesis of intermediate 3-1: 2-bromophenoxazine (10 g,38.3 mmol), iodobenzene (15.6 g,76.6 mmol), pd was weighed out 2 (dba) 3 (1.48g,1.6mmol)，t-Bu 3 P (0.39 g,1.94 mmol), sodium t-butoxide (15.5 g,162 mmol) in a 500mL three-necked flask, 200mL toluene was added to replace nitrogenThe reaction was carried out at 80℃for 12h. Spin-drying, washing with water, and column chromatography (eluting with PE) to obtain white solid with 65% yield. MS (ASAP) =337.0.
Synthesis of intermediate 3-2: preparing a dry 250mL three-neck flask, setting up a reaction device, vacuumizing, and introducing nitrogen; the nitrogen circulation is kept in the reaction bottle, 3-1 (3.0 g,8.9 mmol) is weighed, THF (100 ml) is added, the vacuum pumping and nitrogen introducing are carried out for three times, and the temperature is reduced to minus 78 ℃; to the flask was slowly added dropwise n-butyllithium solution (3.6 ml,8.9 mmol) and after 60min reaction at-78℃1-3 (3.3 g,8.9 mmol) was added rapidly. The reaction system was allowed to slowly warm to room temperature and reacted for 12h. Water was added, extracted with DCM, and after spinning the solvent dry, PE was slurried to a white solid. The yield thereof was found to be 49%. MS (ASAP) = 595.1.
Synthesis of intermediate 3-3: weigh 3-2 (6 g,10 mmol), (Bpin) 2 (3.8g,15mmol)，AcOK(9.8g,100mmol)，Pd(dppf)Cl 2 (0.74g,1.0mmol)，t-Bu 3 P (0.39 g,1.94 mmol) was placed in a 250mL three-necked flask, 100mL of 1, 4-dioxane was added thereto, and the mixture was reacted at 100℃for 12 hours while substituting nitrogen. Spin-drying, water washing, column chromatography (eluent PE: dcm=5:1) gave a colorless oil, yield 77%. MS (ASAP) = 643.3.
Synthesis of Compound 3: 3-3 (6 g,9.3 mmol), 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (3.8 g,14 mmol), K was weighed out 2 CO 3 (12.8g,93mmol)，Pd(PPh 3 ) 4 (1.1 g,0.93 mmol) in a 250mL three-necked flask, 100mL of toluene, 50mL of ethanol, 50mL of water, and replaced with nitrogen were added and reacted at 100℃for 12 hours. Spin-drying, water washing, column chromatography (eluent PE: dcm=3:1) gave a white solid in 43% yield. MS (ASAP) = 748.3.
Example 4
The embodiment provides a silicon-containing organic compound, and the specific synthetic route is as follows:
Figure BDA0003321967110000281
synthesis of Compound 4: 1-5 (10 g,15.5 mmol), 4-chloro-2, 6-diphenylpyrimidine (8.3 g,31.1 mmol), K was weighed out 2 CO 3 (21.3g,155mmol)，Pd(PPh 3 ) 4 (1.8 g,1.6 mmol) in a 250mL three-necked flask, 150mL of toluene, 50mL of ethanol, 50mL of water, and replaced with nitrogen gas were added and reacted at 100℃for 12 hours. Spin-drying, water washing, column chromatography (eluent PE: dcm=3:1) gave a white solid in 56% yield. MS (ASAP) = 747.3.
Example 5
The embodiment provides a silicon-containing organic compound, and the specific synthetic route is as follows:
Figure BDA0003321967110000282
Synthesis of Compound 5: 1-5 (8 g,12.4 mmol), 4-chloro-2, 6-diphenylpyridine (6.6 g,24.8 mmol), K was weighed out 2 CO 3 (17.1g,124mmol)，Pd(PPh 3 ) 4 (1.4 g,1.2 mmol) in a 250mL three-necked flask, 150mL of toluene, 50mL of ethanol, 50mL of water, nitrogen was replaced, and the reaction was carried out at 100℃for 12 hours. Spin-drying, water washing, column chromatography (eluent PE: dcm=3:1) gave a white solid in 53% yield. MS (ASAP) = 746.3.
Example 6
The embodiment provides a silicon-containing organic compound, and the specific synthetic route is as follows:
Figure BDA0003321967110000283
synthesis of Compound 6: 1-5 (8 g,12.4 mmol), 4-chloro-2-phenyl-6-naphthyl-1, 3, 5-triazine (7.9 g,24.8 mmol), K was weighed out 2 CO 3 (17.1g,124mmol)，Pd(PPh 3 ) 4 (1.4 g,1.2 mmol) in a 250mL three-necked flask, 150mL of toluene, 50mL of ethanol, 50mL of water, nitrogen was replaced, and the reaction was carried out at 100℃for 12 hours. Spin-drying, water washing, column chromatography (eluent PE: dcm=3:1) gave a white solid in 47% yield. MS (ASAP) = 796.3.
Example 7
The embodiment provides a silicon-containing organic compound, and the specific synthetic route is as follows:
Figure BDA0003321967110000291
synthesis of Compound 7: 1-5 (8 g,12.4 mmol), 4-chloro-2-phenyl-6-biphenyl-1, 3, 5-triazine (8.5 g,24.8 mmol), K was weighed out 2 CO 3 (17.1g,124mmol)，Pd(PPh 3 ) 4 (1.4 g,1.2 mmol) in a 250mL three-necked flask, 150mL of toluene, 50mL of ethanol, 50mL of water, nitrogen was replaced, and the reaction was carried out at 100℃for 12 hours. Spin-drying, water washing, column chromatography (eluent PE: dcm=3:1) gave a white solid in 42% yield. MS (ASAP) =824.3.
Example 8
The embodiment provides a silicon-containing organic compound, and the specific synthetic route is as follows:
Figure BDA0003321967110000292
synthesis of Compound 8-1: dibenzofuran-3-boronic acid (10 g,47 mmol), 2, 4-dichloro-6-phenyl-1, 3, 5-triazine (10.6 g,47 mmol), K was weighed out 2 CO 3 (32.5g,236mmol)，Pd(PPh 3 ) 4 (5.5 g,4.7 mmol) in a 250mL three-necked flask, 150mL of toluene, 50mL of ethanol, 50mL of water, and replaced with nitrogen were added and reacted at 100℃for 12 hours. Spin-drying, washing with water, and column chromatography (eluent is PE to obtain white solid with yield of 80%. MS (ASAP) =357.1.
Synthesis of Compound 8: 1-5 (8 g,12.4 mmol), 8-1 (8.8 g,24.8 mmol), K are weighed out 2 CO 3 (17.1g,124mmol)，Pd(PPh 3 ) 4 (1.4 g,1.2 mmol) in a 250mL three-necked flask, 150mL of toluene, 50mL of ethanol, 50mL of water, nitrogen was replaced, and the reaction was carried out at 100℃for 12 hours. Spin-drying, water washing, column chromatography (eluent PE: dcm=3:1) gave a white solid, yield 49%. MS (ASAP) = 838.3.
Example 9
The embodiment provides a silicon-containing organic compound, and the specific synthetic route is as follows:
Figure BDA0003321967110000293
synthesis of Compound 9-1: 3-boric acid-9, 9-dimethylfluorene (5 g,21 mmol), 2, 4-dichloro-6-phenyl-1, 3,5 triazine (4.7 g,21 mmol), K was weighed out 2 CO 3 (14.5g,105mmol)，Pd(PPh 3 ) 4 (2.4 g,2.1 mmol) in a 250mL three-necked flask, 150mL of toluene, 50mL of ethanol, 50mL of water, nitrogen was replaced, and the reaction was carried out at 100℃for 12 hours. Spin-drying, washing with water, and column chromatography (eluent is PE to obtain white solid with yield of 84%. MS (ASAP) = 383.1.
Synthesis of compound 9: 3-3 (5 g,7.8 mmol), 9-1 (6.0 g,15.6 mmol), K were weighed out 2 CO 3 (5.4g,38.9mmol)，Pd(PPh 3 ) 4 (0.90 g,0.78 mmol) in a 250mL three-necked flask, 150mL of toluene, 50mL of ethanol, 50mL of water, and replaced with nitrogen gas were added and reacted at 100℃for 12 hours. Spin-drying, water washing, column chromatography (eluent PE: dcm=3:1) gave a white solid in 42% yield. MS (ASAP) = 864.3.
Example 10
The embodiment provides a silicon-containing organic compound, and the specific synthetic route is as follows:
Figure BDA0003321967110000301
synthesis of Compound 10-1: n-phenyl-3-carbazoleboronic acid (5.0 g,17.4 mmol), 2, 4-dichloro-6-phenyl-1, 3,5 triazine (3.9 g,17.4 mmol), K was weighed out 2 CO 3 (12g,87mmol)，Pd(PPh 3 ) 4 (2.0 g,1.7 mmol) in a 250mL three-necked flask, 150mL of toluene, 50mL of ethanol, 50mL of water, and replaced with nitrogen were added and reacted at 100℃for 12 hours. Spin-drying, washing with water, and column chromatography (eluting with PE to give white solid with 89% yield, MS (ASAP) = 432.1.
Synthesis of Compound 10: 3-3 (5 g,7.8 mmol), 10-1 (6.7 g,15.6 mmol), K was weighed out 2 CO 3 (5.4g,38.9mmol)，Pd(PPh 3 ) 4 (0.90 g,0.78 mmol) in a 250mL three-necked flask, 150mL of toluene, 50mL of ethanol, 50mL of water, and replaced with nitrogen gas were added and reacted at 100℃for 12 hours. Spin-drying, washing with water, and column chromatography (eluent is PE: DCM=3:1) to obtainWhite solid, yield 55%. MS (ASAP) = 913.3.
Example 11
The embodiment provides a silicon-containing organic compound, and the specific synthetic route is as follows:
Figure BDA0003321967110000302
synthesis of Compound 11: 1-5 (8 g,12.4 mmol), 4-chloro-2, 6- (3-pyridinyl) -1,3, 5-triazine (7.9 g,24.8 mmol), K was weighed out 2 CO 3 (17.1g,124mmol)，Pd(PPh 3 ) 4 (1.4 g,1.2 mmol) in a 250mL three-necked flask, 150mL of toluene, 50mL of ethanol, 50mL of water, nitrogen was replaced, and the reaction was carried out at 100℃for 12 hours. Spin-drying, water washing, column chromatography (eluent PE: dcm=3:1) gave a white solid in 47% yield. MS (ASAP) = 750.3.
Example 12
The embodiment provides a silicon-containing organic compound, and the specific synthetic route is as follows:
Figure BDA0003321967110000311
synthesis of intermediate 12-1: preparing a dry 500mL three-neck flask, setting up a reaction device, vacuumizing, and introducing nitrogen; the nitrogen circulation is kept in the reaction bottle, 1, 4-dibromobenzene (10 g,42.6 mmol) is weighed, THF (250 ml) is added, the vacuum pumping and nitrogen circulation are carried out for three times, and the temperature is reduced to-78 ℃; to the flask was slowly added dropwise n-butyllithium solution (17.4 ml,42.6 mmol) and after reaction at-78℃for 30min, dimethoxybis (4-t-butylphenyl) silane (15 g,42.6 mmol) was rapidly added. The reaction system was allowed to slowly warm to room temperature and reacted for 12h. Water was added, extracted with DCM, and after spin-drying the solvent, a colorless oil was obtained by column chromatography (eluent PE) in 33% yield. MS (ASAP) = 480.2.
Synthesis of intermediate 12-2: preparing a dry 250mL three-neck flask, setting up a reaction device, vacuumizing, and introducing nitrogen; the nitrogen circulation is kept in the reaction bottle, 1-2 (3.0 g,8.9 mmol) is weighed, THF (100 ml) is added, the vacuum pumping and nitrogen introducing are carried out for three times, and the temperature is reduced to-78 ℃; to the flask was slowly added dropwise n-butyllithium solution (3.6 ml,8.9 mmol) and after 60min reaction at-78℃12-1 (4.3 g,8.9 mmol) was added rapidly. The reaction system was allowed to slowly warm to room temperature and reacted for 12h. Water was added, extracted with DCM, and after spinning the solvent dry, PE was slurried to a white solid. The yield thereof was found to be 52%. MS (ASAP) =707.2.
Synthesis of intermediate 12-3: weigh 12-2 (5 g,7.1 mmol), (Bpin) 2 (2.2g,8.5mmol)，AcOK(7.0g,71mmol)，Pd(dppf)Cl 2 (0.74g,1.0mmol)，t-Bu 3 P (0.39 g,1.94 mmol) was placed in a 250mL three-necked flask, 100mL of 1, 4-dioxane was added thereto, and the mixture was reacted at 100℃for 12 hours while substituting nitrogen. Spin-drying, water washing, column chromatography (eluent PE: dcm=5:1) gave a colorless oil in 82% yield. MS (ASAP) = 755.4.
Synthesis of Compound 12: 12-3 (5 g,6.6 mmol), 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (3.5 g,13 mmol), K was weighed out 2 CO 3 (9.1g,66mmol)，Pd(PPh 3 ) 4 (0.77 g,0.66 mmol) in a 250mL three-necked flask, 100mL of toluene, 50mL of ethanol, 50mL of water, and replaced with nitrogen were added and reacted at 100℃for 12 hours. Spin-drying, washing with water, column chromatography (eluent PE: dcm=3:1) gave a white solid in 51% yield. MS (ASAP) = 860.4.
1.2 preparation of OLED devices
In this embodiment, in the green light device, the host material is selected from GH, HATCN as a hole injection layer material, HT as a hole transport material, GP as an electron blocking layer material, the compounds 1 to 12 of the present application as doping materials (GD) of the light emitting material, ET as an electron transport material, liq (8-hydroxyquinoline lithium) as an electron injection material, and the device structure is ITO/HATCN/HT/GP/GH: GD (8% wt)/ET: liq/Liq/Al.
The structure of the compound involved in preparing the OLED device is as follows:
Figure BDA0003321967110000312
the materials HATCN, HT, GP, GH, GD (ref), ET and Liq are all commercially available or their synthesis methods are all prior art.
The process of manufacturing an OLED device using the above materials is described in detail below by way of specific examples.
Device example 1
The method for manufacturing the OLED device of the present embodiment includes the steps of:
1) Cleaning of an ITO (indium tin oxide) anode layer: cleaning an ITO conductive glass anode layer, then ultrasonically cleaning the ITO conductive glass anode layer for 15 minutes by using deionized water, acetone and isopropanol, and then treating the ITO conductive glass anode layer in a plasma cleaner for 5 minutes to improve the work function of an electrode;
2) Forming a hole injection layer: evaporating cavity injection layer material HATCN with thickness of 30nm on ITO anode layer by vacuum evaporation method, and evaporating at rate
Figure BDA0003321967110000321
3) Forming a hole transport layer: evaporating a hole transport material HT on the hole injection layer by a vacuum evaporation mode, wherein the thickness of the hole transport material HT is 60nm;
4) Forming an electron blocking layer: evaporating an electron blocking layer material GP on the hole transport layer, wherein the thickness of the electron blocking layer material GP is 10nm;
5) Forming a light-emitting layer by vapor deposition on the electron blocking layer, wherein GH is a host material, a compound 1 is a guest material, the mass ratio of GH to the compound 1 is 100:8, and the thickness is 40 nanometers;
6) Forming an electron transport layer: on the luminescent layer, electron transport materials ET and LiQ are evaporated by a vacuum evaporation mode, wherein the mass ratio is 5:5, the thickness is 30nm;
7) Forming an electron injection layer: vacuum evaporating an electron injection layer LiQ on the electron transport layer, wherein the thickness of the electron injection layer LiQ is 1nm;
8) Forming a cathode layer: and vacuum evaporating a cathode Al layer with the thickness of 100nm on the electron injection layer.
Device examples 2 to 12
The conditions were unchanged except that the guest material for the light-emitting layer was selected from the compounds shown in table 1.
Device comparative examples 1 to 2
Guest materials Ref-1 and Ref-2 of the OLED device replace compound 1 in device example 1, with the other conditions unchanged.
The current-voltage (J-V) characteristics of the organic light emitting diodes of examples 1 to 12 and comparative example 1 of green devices were tested using a characterization apparatus while recording important parameters such as efficiency, lifetime, and external quantum efficiency. In Table 1, the luminous efficiency is that the current density is 10mA/cm 2 All of the luminous efficiencies and lifetimes were relative values with respect to the organic light emitting diode of comparative example 1. It can be seen that the efficiency and lifetime of the examples based on the present application are improved to a significant extent compared to the comparative examples. In the embodiment of the application, the silicon-containing organic compound with the structure of the general formula (1) is adopted as the main body material of the light-emitting layer, and other organic compounds are adopted as the main body material of the light-emitting layer in the comparative example, so that the efficiency and the service life of the OLED device prepared based on the compound of the application are greatly improved.
TABLE 1
Figure BDA0003321967110000322
Figure BDA0003321967110000331
The technical features of the above-described embodiments may be arbitrarily combined, and all possible combinations of the technical features in the above-described embodiments are not described for brevity of description, however, as long as there is no contradiction between the combinations of the technical features, they should be considered as the scope of the description.
The above examples merely represent a few embodiments of the present invention, which facilitate a specific and detailed understanding of the technical solutions of the present invention, but are not to be construed as limiting the scope of the invention. It should be noted that it will be apparent to those skilled in the art that several variations and modifications can be made without departing from the spirit of the invention, which are all within the scope of the invention. It should be understood that, based on the technical solutions provided by the present invention, those skilled in the art may obtain technical solutions through logical analysis, reasoning or limited experiments, which are all within the scope of protection of the appended claims. The scope of the patent of the invention should therefore be determined with reference to the appended claims, which are to be construed as in accordance with the doctrines of claim interpretation.

Claims (10)

1. The silicon-containing organic compound is characterized in that the structure is shown as a general formula (1):
Figure FDA0003321967100000011
wherein:
X 1 、X 2 、X 3 are independently selected from CR 5 Or N, and X 1 、X 2 And X is 3 At least one of which is selected from N;
Ar 1 、Ar 2 each independently selected from a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, an alkyl group having 1 to 30 carbon atoms;
R 1 、R 2 、R 3 、R 4 、R 5 each occurrence is independently selected from: -H, -D, linear alkyl having 1 to 20C atoms, linear alkoxy having 1 to 20C atoms, linear thioalkoxy having 1 to 20C atoms, branched alkyl having 3 to 20C atoms, cyclic alkyl having 3 to 20C atoms, branched alkoxy having 3 to 20C atoms, cyclic alkoxy having 3 to 20C atoms, branched thioalkoxy having 3 to 20C atoms, cyclic thioalkoxy having 3 to 20C atoms, silyl, keto having 1 to 20C atoms, alkoxycarbonyl having 2 to 20C atoms, aryloxycarbonyl having 7 to 20C atoms, alkenyl having 1 to 20C atoms, carbamoyl, haloformyl, formyl, cyano, isocyano, thiocyanate, isothiocyanate group Hydroxy, nitro, -CF 3 -Cl, -Br, -F, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms, or a combination of these groups;
n is selected from 1, 2, 3, 4 or 5;
m is selected from 1, 2, 3 or 4.
2. The silicon-containing organic compound according to claim 1, wherein the structure of the silicon-containing organic compound is represented by general formulae (2-1) to (2-4):
Figure FDA0003321967100000012
3. the silicon-containing organic compound according to claim 1, wherein Ar 1 、Ar 2 Each occurrence is independently selected from the group consisting of:
Figure FDA0003321967100000021
wherein:
X 4 each occurrence is independently selected from CR 6 Or N;
Y 1 are respectively and independently selected from CR 7 R 8 、NR 9 、SiR 7 R 8 、O、S、Se、S＝O、S(＝O) 2 Or PR (PR) 9 ；
R 6 、R 7 、R 8 、R 9 Each occurrence is independently selected from: -H, -D, a linear alkyl group having 1 to 20C atoms, a linear alkoxy group having 1 to 20C atoms, a linear thioalkoxy group having 1 to 20C atoms, a branched or cyclic alkyl group having 3 to 20C atoms, a branch having 3 to 20C atomsChain or cyclic alkoxy, branched or cyclic thioalkoxy having 3 to 20C atoms, silyl, keto having 1 to 20C atoms, alkoxycarbonyl having 2 to 20C atoms, aryloxycarbonyl having 7 to 20C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, thiocyanate, isothiocyanate, hydroxy, nitro, -CF 3 -Cl, -Br, -F, -I, a substituted or unsubstituted aromatic or heteroaromatic group having 5 to 20 ring atoms, an aryloxy or heteroaryloxy group having 5 to 20 ring atoms, or a combination of these groups.
4. The silicon-containing organic compound according to claim 3, wherein R 6 、R 7 、R 8 、R 9 Each occurrence is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 10C atoms, a branched or cyclic alkyl group having 3 to 10C atoms, cyano, nitro, -CF 3 -Cl, -Br, -F, -I, a substituted or unsubstituted aromatic or heteroaromatic group having 6 to 10 ring atoms.
5. The silicon-containing organic compound according to claim 4, wherein Ar 1 、Ar 2 Each occurrence is independently selected from the group consisting of:
Figure FDA0003321967100000022
Figure FDA0003321967100000031
wherein: * Representing the ligation site.
6. The silicon-containing organic compound according to claim 3, wherein Ar 1 Selected from the group consisting of
Figure FDA0003321967100000032
Ar 2 Selected from->
Figure FDA0003321967100000033
7. The silicon-containing organic compound according to any one of claims 1 to 6, wherein R 1 、R 2 Each occurrence is independently selected from: -H, -D, straight chain alkyl having 1 to 10C atoms, branched alkyl having 3 to 10C atoms, cyclic alkyl having 3 to 10C atoms, silyl, cyano, isocyano, hydroxy, nitro, -CF 3 -Cl, -Br, -F, a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 10 ring atoms, or a combination of these groups.
8. A mixture comprising the silicon-containing organic compound according to any one of claims 1 to 7, and at least one organic functional material selected from a hole injecting material, a hole transporting material, an electron injecting material, an electron blocking material, a hole blocking material, a light-emitting body, a host material, or an organic dye.
9. A composition comprising the silicon-containing organic compound according to any one of claims 1 to 7 or the mixture according to claim 8, and at least one organic solvent.
10. An organic electronic device comprising the silicon-containing organic compound according to any one of claims 1 to 7, the mixture according to claim 8, or a functional layer prepared from the composition according to claim 9.
CN202111249409.3A 2021-10-26 2021-10-26 Silicon-containing organic compounds, mixtures, compositions and organic electronic devices Pending CN116041380A (en)

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